


Flying Friendly

by saltandbyrne



Category: Supernatural
Genre: Airplanes, Bottom Castiel, Butt Plugs, Double Penetration, M/M, Multi, Past Dean/Everyone, Past Sam/Everyone, Pilots, Plot What Plot/Porn Without Plot, Sam and Dean are big sluts, Sibling Incest, Sneakiness, Threesome - M/M/M, Top Dean, Top Sam
Language: English
Status: Completed
Published: 2013-12-31
Updated: 2013-12-31
Packaged: 2018-01-06 20:18:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,987
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1111088
Author URL: https://archiveofourown.org/users/saltandbyrne/pseuds/saltandbyrne
Summary: <blockquote class="userstuff">
              <p>Castiel likes order, most of the time, but there are days when all he wants is to make a mess of everything. As Sam and Dean kiss each other over his shoulder, Castiel sighs with contentment.  This is a glorious mess.</p>
            </blockquote>





	Flying Friendly

Things on earth can get messy.

 

Up here, where the clouds break apart into thin white threads and the ground spreads out like a handmade quilt, up here, Castiel knows the rules. He makes the rules, really. It's one of the perks of being in charge.

 

“Warm towel, madam?” Castiel knows the perfect amount of space to leave as he leans in, the steam wafting from the neatly-rolled towel clutched between his tongs. The incline of his head, the angle of his hands, the concerned-but-not-fake smile delicately curling his lips – all these things are measured in the same precise, studied way that has gotten Castiel where he is today.

 

“You're a doll,” croons Marjorie Koonings, O'Hare to Geneva, one-hour layover Geneva to La Choux-de-Fonds, likes small dogs and modern art, hates tree nuts and the color fuchsia. “And get me another Riesling, wouldn't you?”

 

Castiel already has one tucked discreetly into his pocket, as though it were a thoughtful gift from a knowing friend and not an easy guess. At least she isn't a mean drunk.

 

“You must have the cutest boyfriend,” she whispers warmly, friends already after a 12-hour flight.

 

Castiel just smiles like it's the most amusing thing he's ever heard. He's spared more requests or inquiries about his sex life as he hears the soft chime of the PA system.

 

“This is your captain speaking.”

 

He retreats to the small beverage area and pulls the curtain closed behind him. Everything is in order, the small serving trays stacked neatly in their slotted shelf, the artfully-arranged basket of organic snacks ready to be offered to his charges. Castiel smiles as he hears the captain continue.

 

“We'll be starting our descent to Geneva in approximately fifteen minutes. We'll be asking all passengers to secure their seatbelts and return their seats to the upright position. On behalf of the entire flight crew, thank you for choosing Continental.”

 

Castiel smiles to himself, fussing over the air-dried apple chips and making sure the multigrain crisps are visible. Captain Dean Winchester always landed smooth and left on time, with a star-eyed train of stewards, stewardesses, passengers and assorted airport personnel behind him. Castiel takes a moment to adjust the creaseless blue ascot at his neck. He'd still be within regulation if he wore the tie, of course, but Balthazar always wears the tie and Castiel likes standing out. He knows it brings out his eyes.

 

Their landing is perfect, as always, and Castiel smiles as Dean thanks everyone for joining him today. As they stand next to one another at the farewell line, shaking hands with passengers and waving at excited children, Castiel lets his shoulder brush against Dean's. From the corner of his eye he catches the bob of Dean's adam's apple as he swallows, and Castiel smiles as a little girl waves at him. He crouches down to hand her a plastic pin and slowly rises up as she claps with glee and lets her father affix it to her sweater. Castiel angles himself just so, letting more of his hip slide up along Dean's leg than is strictly necessary. Castiel can hear the rush of breath Dean lets out as he smiles at the departing passengers.

 

Saying that Dean Winchester has a reputation implies some sort of exaggeration or rumor-mill grandiosity. Castiel prides himself on knowing his crew. He's chief steward, after all, and managing the diverse talents of an international flight crew could be a tricky business. Casey and Cassie never flew together if Castiel had anything to say about it, and Victor and Bela could only be civil if one of them got stuck in coach. At the root of so many of Castiel's scheduling machinations sat Dean Winchester, he of the huge dick, the best tongue in the western hemisphere, the ass that doesn't quit, and the perkiest nipples ever known to humanity according to Casey, Cassie, Victor and Bela respectively.

 

Castiel empties the seatbacks and triple-checks his stock lists as the other stewards and flight crew make their way off the plane. Dean lingers as well, his eyes roving over Castiel's body as he stretches to reach the overhead compartments and bends to retrieve abandoned fleece slippers. Castiel takes his time.

 

Dean has tried before, and Castiel has brushed him off with a variety of polite excuses that seem to leave Dean more spellbound each time. Castiel knows that the best thing to give the man who gets whatever he wants is a good dose of restraint. It only seemed to whet Dean's appetite, and each flight they had together felt a little more charged, the perfunctory goodbyes of the farewell line a little more tense.

 

Castiel straightens up, smoothing down his vest and resting one hand on either side of the aisle. This is Castiel's kingdom, and Castiel has a plan.

 

He looks Dean dead in the eye as he walks down the aisle, his shoulders back and his head held high. Dean's face is a sight, his usual swagger still arching his eyebrows up while his mouth purses with well-hidden confusion. His eyes widen as Castiel pulls a neatly-creased slip of paper from his vest pocket.

 

“I'll be in Phoenix next Tuesday.” Castiel slips the paper into Dean's front pocket, letting his fingertips trail over the weave of his suit. “You'll find a key card waiting at the desk.”

 

Dean watches Castiel up the entire boarding ramp, his mouth open with shock as Castiel wheels his small suitcase behind him.

 

*

 

“Certainly, Mr. Finch, it would be my pleasure to make you a new coffee.” Castiel smiles as he accepts the full cup, marveling that anyone had the gall to request Equal and then complain about the taste.

 

He stands at the beverage station, stirring a half-spoon of sugar into Mr. Finch's black coffee. He looks up as he hears the familiar chime.

 

“This is your captain speaking.”

 

Castiel stirs the spoon and smiles to himself.

 

“We'll be starting our descent to New York in about fifteen minutes. We'll be asking everyone to close their seat-trays and return their seat to the upright position and keep your seatbelts on during our landing. On behalf of everyone at Continental, we thank you for flying with us today.”

 

Captain Sam Winchester is known for his steady hands during turbulence and his charming smile. He is perhaps most famous for having an even bigger dick than his brother.

 

Sam isn't as openly flirtatious as Dean and he seems prone to discretion rather than the cockpit blowjobs and bathroom stall hijinks Dean favors, but he had a reputation of his own.

 

“He's like a wild animal,” Madison had cooed at an airport bar in San Francisco, hiking her skirt up to show Jo the palm-shaped bruise on her ass. Castiel had looked the other way out of politeness and a general disdain for drunken bragging, but only after he'd caught Jo's knowing nod.

 

“I know, right? He bit me so hard I almost passed out,” Jo had sighed. “Well, I probably did pass out after, like, the fifth orgasm I had, Christ, the mouth on him.”

 

Bela didn't need a single drink to brag about anything, entertaining six different crew members with her point-by-point comparison of the penises Winchester and toasting to Annie, who had once slept with Sam, Dean, and Sam again in the same week.

 

Castiel listens politely, gleaning everything he can about the brothers. Sam was longer but Dean was thicker, Dean would let someone suck his dick all night while Sam went straight for sex, Dean was a cuddler while Sam got all gentlemanly and escorted them out to hail a cab. They both ate pussy like it was their job and apparently they both gave a rim job that made Kevin Tran see God. They both slept with men and women, but Dean was the only one who bottomed, although according to Victor he was a bossy one. Sam was rough, a hair-puller, a biter, a scratcher who liked it up against the wall or from behind. Dean was slow, liked kissing and messy blowjobs, liked lying on his back and letting his partner ride him while he got them off.

 

Most of Castiel's crew mates have fucked one of them, and a lot of them have fucked both of them. But as far as Castiel can tell, no one has ever been with both of them at the same time.

 

Castiel has a plan.

 

Sam's overtures were less obvious than Dean's, but he hadn't tried to get in Castiel's pants any less. Sam mentioned nice restaurants and movies he wanted to see, and Castiel politely expressed his regret that he was busy, but thank you. He always caught Sam staring out of the corner of his eye, especially today. The ascot might bring out his eyes but the tight pants made his ass look amazing.

 

The New York landing is smooth. Castiel gives Mr. Finch a saccharine smile as he departs. He notes with satisfaction that Sam doesn't seem interested in Gabriel's advances or Ruby's sly flirtation. Sam shakes hands and smiles until the plane is empty. Castiel remains, checking off his stock list and bending down to reach a balled-up pair of disposable socks someone had left behind.

 

Sam's watching him, Castiel can feel it. Just like his brother. Castiel straightens himself up and smiles.

 

“I'll be in Phoenix this Tuesday.” He slips the piece of paper into Sam's pocket, letting his fingers press into Sam's chest. “I'll leave a key card at the desk.”

 

“I'll be in Phoenix, too,” Sam says, like Castiel doesn't know this, like he hasn't tracked Sam and Dean's flight schedules for weeks. He isn't sure if Sam and Dean had planned to be in the same city or if it was just a happy coincidence, but it suited Castiel just fine.

 

“I know.” Castiel drums his fingers against Sam's chest and smiles. Sam starts to say something as Castiel turns, but Castiel doesn't hear it as he disembarks, the wheels of his suitcase clicking behind him.

 

*

 

Castiel likes order.

 

He refolds the towels in the bathroom until the seams face inwards. They're exceptionally soft, as well they should be. Castiel was generally sensible with his money, but if he's going to splurge on anything, it's this. He's spending all night in this room one way or another.

 

Castiel smoothes the bedspread and re-fluffs the pillows, lining the edges up with each other. He'd gotten the room with two king-sized beds. The view isn't anything to write home about so Castiel keeps the ostentatious curtains drawn. He moves the bible discreetly tucked in the bedside drawer to a closet shelf. He needs that drawer for supplies, and it ruffles his sense of decorum to get lube stains on a book.

 

He's not wearing the ascot today, but he is wearing his uniform pants and a crisp white shirt rolled up at the elbows. It's as close to casual as he gets. He checks his hair in the mirror, satisfied that it's behaving well enough for now. He indulges for one moment, shifting a little and clenching his muscles to feel the soft pressure of the plug inside him. He likes the way his eyes flare at the sensation.

 

Castiel has spent months planning this evening, and if he's learned one thing, it's that the best plans are the ones with a back-up plan. Even if things don't work out, Castiel will still have a night to himself with a chilled bottle of Perrier Jouet and a well-curated selection of sex toys.

 

The snick of the key card in the door turns Castiel's head. The clock reads 7:16, so Castiel is ready as Sam opens the door and peers inside.

 

Sam has just arrived from a flight, so he's looking tired around the eyes but he's still wearing his full pilot's uniform. Castiel thanks heaven for small favors and leads Sam inside, pouring him a flute of champagne and making small talk about Sam's trip from Ontario.

 

“Nice.” Sam sinks into one of the armless chairs flanking the windows and sips his drink.

 

“Well, if you're going to treat yourself, you might as well have the best.” Castiel slides into Sam's lap, loving the way Sam's lips part and his eyes slant up as Castiel toys with the top button of his shirt.

 

Sam's hands slide over his back, circling around Castiel's waist before cupping over his ass. Castiel's skin goes prickly as the toy inside him shifts.

 

“Been trying to get your attention for a while now, Cas.” Sam pulls him in closer, shifting his hips so Castiel can feel the swelling line of his cock brush up against him.

 

“Like I said,” Castiel sighs, licking his lips and hooking his foot around the chair to wriggle down and make Sam's lip curl back. “I like the best.”

 

Sam smiles, and it's so lazy and pleased and completely like his brother Castiel feels a pleasant tension strum through him. He leans down, wrapping his arms around Sam's shoulders and kissing him roughly. Sam makes a surprised sound before kissing him back, all nips of teeth and the rasp of trans-continental stubble against Castiel's lips. Sam gives his ass a rough squeeze before tugging impatiently at Castiel's shirt, pulling it out of Castiel's waistband and growling at each button like it's a personal offense.

 

In a neat series of simultaneous events, Castiel glances at the clock and registers that it's 7:29, Sam ruins the last button of Castiel's shirt and sends it sailing across the room, and the door make a soft click as Dean arrives. Castiel smiles around Sam's confused noise and slowly turns around.

 

Castiel has seen Dean laughing and cajoling, frustrated and tired, but he's never imagined that Dean would look so handsome when he's perplexed. His eyes flit between Castiel's bare back and Sam's hand scooped over the curve of his ass before he softly closes the door behind him.

 

“Got a little scheduling problem, Cas?” Dean isn't wearing his uniform, but he still looks good as he crosses his arms over his chest and leans against the wall. The leather stretches nicely as he arches an eyebrow, his lip curling up in a bemused grin.

 

Bemused is good. Bemused isn't horrified, or offended, or panicked, or any of the other facial expressions that lead to Plan B.

 

Castiel extricates himself from Sam's lap and stretches, carefully watching the way Dean licks his lips and tilts his head, his eyes sliding over Castiel's chest, which Castiel knew they would, and landing right on the healthy bulge currently tenting Sam's uniform slack, which Castiel had really, really hoped they would.

 

There's a crackle in the air, a nervous kind of tension that makes Castiel's skin itch as he saunters over to the ice bucket and pours Dean a drink. Castiel doesn't need any extra attention, not as he slowly sinks the bottle back into the bucket and catches sight of the heated look on both brothers' faces. Sam hasn't moved, his legs spread open and his lips candy-pink. He looks across the room at Dean with an expression that would make Castiel hard just to see it.

 

Dean still looks amused, but each blink of his eyes adds an edge of hunger that makes Castiel bite his lip. Dean shrugs his jacket off and tosses it carelessly onto the desk before accepting Castiel's flute of bubbly. He takes a deep sip, closing his eyes and humming at the taste before setting it down on the leather desk blotter. Castiel feels a thrill run up his spine. The condensation is going to ruin the leather.

 

Dean cracks his neck from side to side, keeping his eyes fixed on Sam. He licks his lips, slowly, letting the tip of his tongue play over the left side of his mouth. Planting his feet and tilting his head with a sly grin, he raises an eyebrow at Sam before turning the full force of his gaze on Castiel. Anna was right. It is absolutely panty-melting. Dean keeps one hand hooked in his belt, his fingers hovering suggestively over his crotch. He brings his other hand up and crooks two fingers towards himself, beckoning Castiel closer.

 

Castiel serves privileged, arrogant assholes for a living, and he's never seen anything close to the cocksure set of Dean's hips. He's also never responded to a beckoning hand gesture so quickly before.

 

Castiel shivers when Dean strokes his fingers up his arm, his eyes fluttering shut as he leans towards the inexorable pull of Dean. Just as Castiel suspected, Dean leads with his lips, letting the plush swell of his lower lip drag across Castiel's. He teases his tongue in slowly, tracing the tip over Castiel's own before he draws it back in to make Castiel chase him. Castiel is happy to oblige.

 

Dean molds to him slowly, the drag of his fingers up Castiel's arms unfolding to wrap around his biceps and pull him closer. His chest presses against Castiel's, the buttons of his shirt digging into Castiel's skin as his hips roll forward. Castiel groans softly as he feels Dean's crotch brush against his, the fly of his jeans bulging against Castiel's own hard-on.

 

Dean's hands skate up his arms, leaving goosebump trails in their wake as he slides one hand into Castiel's hair and molds the other over Castiel's cheek. It's possessive and gentle and Castiel leans his head in just to feel the soft tug of Dean's fingers through his hair. Castiel's hands are brushing against the broken-in material of Dean's shirt when he feels two more hands slide around the cut of his waist.

 

Sam crowds in behind him, and Castiel wonders how either of them can fit in a cockpit. Between the two of them there's hardly any air to breathe, any space to move and Castiel flexes around the toy in his ass as Sam palms his hipbones and pulls him back. Sam's cock is a hard line against his ass, hot and insistent as Sam grinds against him.

 

Dean growls so softly Castiel can feel it more than he can hear it, a rumble against his chest as Dean stakes a claim with his tongue. He pulls off with Castiel's lip sucked between his teeth and a flex of his hips that makes Castiel feel giddy as he absurdly thinks of Bela's bar-room bragging. Thicker, indeed.

 

Sam's hand closes over his hip and squeezes, his chest pulling away from Castiel's bare back as Castiel turns to him. Unwilling to sacrifice the pleasure of both their cocks against him, Castiel turns at his waist to meet Sam's kiss. There are no soft lips here, just a filthy sweep of his tongue like he's licking the taste of Dean out of Castiel's mouth.

 

There's a thin string of spit webbing from Sam's lips to Castiel's as Sam faces Dean. Castiel can feel them both breathing against him, broad chests caging him in and they're both so warm, there's sweat pebbling on his neck. Dean smiles, raising an eyebrow at Sam.

 

“Been a while since we've done this.”

 

“Cincinnati?”

 

“Sydney.”

 

“Oh, right,” Sam hums, releasing his hold on Castiel's hip to trace it over his arm in an echo of Dean's soft strokes. Dean's hand glides down to strum along the cut lines of Castiel's ribcage, pressing over each one with Sam's roughness and Castiel shivers. There are two hands unaccounted for.

 

Castiel will be perfectly, utterly satisfied if Sam and Dean both fuck him, take turns watching while they wring him out and call it a night. But Castiel has always had high hopes and even more, he has a suspicion. He's only seen them together at a scarce handful of social events and company parties, but Castiel can glean more about a person in thirty seconds than a shrink can pull out in a year. It's what makes him so good at what he does.

 

Castiel looks back and forth between both brothers, blinking slowly and arching his eyebrow with coy impatience. He knows they're all waiting for it, and the unspoken look Sam and Dean share makes Castiel tingle with the deep, cock-throbbing satisfaction of being right. With Sam's sloe-eyed chagrin and Dean's molasses smirk they both shrug and lean in to each other while Castiel holds his breath.

 

Castiel likes order, most of the time, but there are days when all he wants is to make a mess of everything. As Sam and Dean kiss each other over his shoulder, Castiel sighs with contentment. This is a glorious mess.

 

“Fuck,” Castiel groans, and Sam and Dean both look at him with surprise. It's still more polite than the “I fucking knew it!” that had been dancing on the tip of his tongue so Castiel just throws off a shrug of his own.

 

“Please do that again,” Castiel supplies, slipping out of their clutches and shivering at the chill of the air-conditioning against his bare voyeur's skin. He catches a slip of pink tongue between them as they oblige his request and draw together, Sam's hands cutting rough over Dean's back as they wrestle out of their shirts.

 

Dean pulls off of Sam's kiss and drags his lips over the dip in Sam's chin, turning their heads until they're both staring hungrily at Castiel. Flushed and full, Castiel's cock twitches like a willing victim of their benevolent predation and he palms himself over his pants.

 

“You know you've got a reputation, Cas,” Dean lilts, drawing out his shortened name and curling away from Sam with too much grace for someone sporting a huge hard-on. He reaches out to drag Castiel belt-first until he's pressed up against his side, his fingers playing over the smooth ridges of Castiel's zipper.

 

“Kind of a prude,” Sam agrees, cocking his head to the side while Dean catches the head of his zipper between his fingers. “Kind of stuck up.” Sam slides his own belt out and lets it fall with a muffled thump against the carpet. “Kind of uptight.”

 

Dean opens his fly and sighs out a gruff laugh against his neck, his breath tickling hot against Castiel's skin as his pants pool graciously around his ankles.

 

“Now I've always thought, and correct me if I'm wrong,” Dean drawls, toeing Castiel's pants out of the way. “That it's the uptight ones who like to get the dirtiest.” He gives Castiel a rough squeeze through his boxers with the last word, soaking a fresh wet spot into the material and making Castiel groan.

 

Dean grins and shucks his own pants with a studied efficiency that shouldn't make Castiel feel so excited. Castiel values mastery the way others value charm and big dicks, although none of those qualities seem to be lacking in the charged air of the hotel room. Sam follows suit and leaves his slacks in a navy puddle as he slides in next to Castiel.

 

“That's what I've always thought,” Sam says, clucking his tongue and looking down at the heavy jut of Castiel's dick. Castiel is halfway through the absurd thought that they're both wearing the same exact brand of boxer briefs, that maybe they forget and put each other's on sometimes after they fuck and he gasps, a sound he's not fond of making, when they both sink to their knees in perfect unison. They fly expensive, delicate machines for a living, so it's not like it should surprise him that they're so perfectly choreographed, but Castiel still looks down wide-eyed and momentarily speechless.

 

Walking on his knees with his cock tenting his boxers, Dean has no business looking so smooth as he edges behind Castiel. A mouth molds to his hip, Sam's by the rough bite of it, while Dean's breath teases along the dimples at the base of Castiel's spine. Fingers curl into the flat elastic of his waistband, two sets of hands grasping and tugging and dragging along his skin until Castiel's toes curl and he sighs. He barely feels the soft cotton of his underwear settling around his feet, too distracted by the shock of cold air against the blood-hot throb of his dick and the jarring, perfect dissonance of Dean delicately kissing down the curve of his ass while Sam nips a trail down his hip. He spreads his legs without thinking, gasping at the sudden movement inside him and the deep groan Dean makes. Castiel still has the ace up his sleeve.

 

“Christ.” Dean's thumb skates along the edge of the plug nestled deep inside him, his other hand pulling Castiel further open. “Sam.”

 

Castiel still possesses enough dignity not to whine when Sam, his mouth so close to Castiel's dick he can feel the warm rush of his breath, pulls back.

 

“Told you he'd be one of the dirty ones.” Dean digs his fingers into either side of Castiel's ass, pulling wide as Sam leans over and groans.

 

“Fuck, Cas.”

 

God, it should be humiliating, spread open for both of them to inspect but it just makes him burn hotter, makes him squirm into Dean's hands just to feel that teasing graze over his sweet spot like a promise.

 

“Told you he's a bottom.” Dean must be smirking, or something close to it as the soft catch of his overseas-flight stubble drags along Castiel's skin. Sam looks up at him, eyes dark and stormy like something no sane person would want to fly through and Castiel just nods, lip caught between his teeth to keep him steady.

 

Sam smiles, slow and hungry before he snakes his tongue out, dragging it up the underside of Castiel's cock. Contact after so long, after so much charged anticipation and wet promise makes Castiel jump, bucking up towards Sam's pink smirk and hissing at the sweet, stinging pull of Dean's fingers, clamped firmly around the base of Castiel's toy. It catches on his rim, just enough to make his skin tingle and his tongue thicken too much to say anything coy.

 

Sam stands up first, leaving his boxers behind and pressing into Castiel before he can get a good look at Sam's dick, not that he can't feel it nudging at his stomach.

 

“That what you want, Cas?” Sam purrs, all bated breath as he circles his hips, dragging his cock along Castiel's skin. Hot flesh and the tickling, wet prickle of precome leave a trail of gooseflesh as Sam noses along his neck. “Want this?” Sam presses in, smiling as he grinds his cock against Castiel and it should be arrogant and irritating, the sort of locker room bravado that Castiel normally finds so distasteful, but Castiel just nods his head and searches half-blind for Sam's mouth.

 

It's only Sam's tongue swirling around his that muffles the moan Castiel lets out as Dean slides up behind him, bare and thick and so hot against him. Dean's cock slots between the cleft of Castiel's ass, each small circle of his hips pressing Castiel's plug deeper inside him.

 

“I think he wants to get fucked.” Dean breathes against him, dragging his teeth along the hot ridge of Castiel's ear, flicking his tongue after it. His hand slides over the cut of Castiel's waist, slowly working its way between Castiel and Sam one skin-dragging inch at a time. “I think you need to get fucked, don't you, Cas?”

 

Sam's mouth drags along the wing of Castiel's jaw, lips kiss-wet and hot against him. Castiel tilts his head back, finding Dean's shoulder just as Dean's hand closes over Sam's cock, fingers stretching until he's got Castiel's as well.

 

“Want us to take turns, Cas?” Dean strokes up, squeezing out a fresh drop of precome from Castiel's dick that slips against the shaft of Sam's cock. “Fuck you over and over, come in and take you sloppy after we're both done?”

 

“Flip a coin,” Sam mumbles, his lips trailing off of Castiel's skin. “See who gets to fuck you first?”

 

“No.” Castiel finally finds his voice, hips pumping up into Dean's hand as Sam stills against him.

 

“I want you both.” Castiel snakes his arm up, curving it behind Dean's neck to draw him in for a kiss. He sucks Dean's bottom lip between his teeth, biting softly before he turns his head for Sam. He takes his time, letting himself savor the heat of them pressed against him before he pulls off of Sam's mouth with a soft pop.

 

“Together.”

 

He can't see Dean's face but he's sure it's a mirror of Sam's arch grin. Sam's eyebrows rise up to mingle with the soft shag of his hair as his hand wanders over Castiel's hip, tracing down to the cleft of his ass. His index and middle fingers slot over the flared base of Castiel's plug, rubbing back and forth while his knuckles graze against Dean's cock.

 

“Think you can handle that?” Dean's hand tightens around Castiel and Sam's cocks, sliding down until Castiel's foreskin stretches back and he shudders.

 

“I know my own body,” Castiel says, as tersely as he can manage when Dean's licking up the side of his neck and Sam's chuckling warmly against his chest.

 

“I bet you do.” Sam urges them all towards the bed, feet tangling together and hands roaming everywhere. Dean's knees hit the side of the mattress before he sinks down, turning Castiel around to straddle his lap.

 

Castiel's toes curl into the rich threadcount sheets as Sam kneels down behind him. Broad hands land on either side of Castiel's ass, exposing the slick black toy moving inside him.

 

“So fucking hot,” Sam murmurs, circling the pad of his index finger around the rubber base. “Waiting for us, fucking yourself good and ready.” He grasps the flared base firmly and tugs, drawing it out just to let it sink back into the grasping pull of Castiel's body. “We've never double-stuffed a guy before, have we?”

 

Dean arches a thoughtful eyebrow and reaches up to cup Castiel's face. “Be gentle, baby, it's my first time,” Dean drawls, pouting his lips as Castiel rolls his eyes.

 

“It's not mine,” Castiel drawls back, smirking at the brief, wide-eyed look Dean gives him before he recovers.

 

“Got ourselves an expert,” Sam huffs, his lips brushing over Castiel's back as he grips the toy again and pulls it out, firmly this time. It's the biggest one Castiel owns and he groans at the stretch, at the shudder of muscles as Sam carefully works it out. It slips past his rim, leaving a warm trail of lube behind, waiting and ready for Sam to sink his fingers in to the second knuckle and groan.

 

“Fuck, he's so open.”

 

Castiel wouldn't have thought that he'd like being talked about like he isn't there but there's something about the matter-of-fact way the brothers play off each other that makes Castiel feel dizzy.

 

“Yeah?” Dean keeps his hand cupped on Castiel's cheek, brushing his thumb over Castiel's lips. “Think you can take me?”

 

“God, yes,” Castiel says impatiently, turning his face to nip at Dean's thumb. He's not sure what he wants more, sweet relief from the fever-burn of emptiness inside him or for it to never end.

 

“Greedy,” Dean chides, smirking. Castiel rolls his hips, grinding his own hard-on against Dean's stomach and giving what he hopes is a plaintive groan.

 

“I got you,” Sam murmurs behind him, bracing his big hand over Castiel's hip as he reaches for the tastefully-arranged assortment of condoms spread out on the bedside table. The rip of foil, the snick of the lube bottle and Castiel feels Sam's fingers ghost past him as he rolls a condom down Dean's cock and smears him slick.

 

“Ready?” Dean reaches around and nudges the head of his dick against Castiel's hole, throb-hot and ready. Bracing himself on Dean's shoulders, Castiel arches his back and sinks down until he can feel the fat head of Dean's cock breach him. He goes in easy, inch by inch with Sam's fingers skirting around the juncture of their bodies.

 

“Look at you, just fucking take it,” Sam marvels, running his lips along the undulating curve of Castiel's waist.

 

Dean's lips close around Castiel's nipple just as Sam slips a finger in beside his brother's dick and Castiel grits his teeth, feeling the flare of sensation as Sam stretches him further. Dean licks teasing swipes across Castiel's chest, making his skin prickle and flush in his wake. Castiel feels static-hot all over, the pleasure of Dean's gentle hands and firm mouth mingling with the too-good ache of Sam's fingers.

 

“Please,” Castiel moans, turning back to slant his eyes at Sam. He can feel his lips throbbing, stubble-burnt from Dean's kisses and he wonders what he looks like to Sam, spread wide like this, face flushed but polite to the end.

 

“Yeah, I got you.” Sam nods, his eyes fox-slit and dark, a perfect counterpoint to Dean's wide-eyed look of anticipation as he lies back on the bed. Castiel leans over him, making room for Sam behind him as he hears the rustle of Sam prepping himself. The bed dips and Castiel feels blunt pressure at his hole, Sam's hand steadying at his waist while he murmurs a stream of meaningless filth. Dean's breath is shallow, his lip bitten between his teeth as Sam slowly presses inside, and Castiel knows Dean's holding himself back. Rumor has it he never comes first and Castiel is happy to keep his record unblemished.

 

Dean seems to sense Castiel's line of thought as he reaches down to stroke lazily at Castiel's cock, not so much to get him off but as a distraction. With Dean on the bottom he doesn't get to control much of the action, but the stunned look on his face as Sam starts to move against him says he doesn't mind.

 

Sam starts up fast and doesn't stop, which is no surprise to Castiel. Soon it's all too much, too many slips and slides and grunts and sighs against him for Castiel to keep it straight, until it's all just feeling and Castiel lets himself lose control.

 

He comes first, shooting over Dean's clenched hand and biting his own lip so hard he tastes copper. It's all a blur after that, just big hands holding him and hot mouths marking his skin up like a family crest. He thinks Sam comes before Dean, or maybe he just makes more noise. Castiel lets them guide him down to curl between them, their arms and legs tangling over him.

 

Even his own orgasm seems secondary to the victorious feeling of Sam and Dean on either side of him, bodies sinking into sleep and the overstuffed mattress. Castiel looks at them both, slack-jawed in sleep and still impossibly handsome. Castiel closes his eyes, exhausted and utterly satisfied with the success of a well-laid plan borne to fruition.

 

He wakes up at 6 AM sharp, his own sense of time more reliable than any alarm clock. It seems a shame to leave both Winchesters in bed, especially with the tempting promise of Dean's morning wood and the way Sam sleeps ass-up and legs spread. But Castiel has a plan, and he knows that this can be more than a one-time thing if he plays his cards right.

 

After dressing quietly, brushing his teeth and combing his hair into submission, Castiel pulls a small card from his pocket and leaves it on the dresser. It's a business card for the nicest hotel within fifteen minutes of LaGuardia Airport. Written neatly in Castiel's loose script is a date three weeks in the future and “See you both soon.”

 

Castiel would bet his ascot that they'll both be there. He quietly closes the hotel door behind him and heads for the elevator, the wheels of his rolling suitcase clicking behind him.

 

 

 

 

 

**Works inspired by this one:**

  * [[Podfic] Flying Friendly](https://archiveofourown.org/works/4879171) by [RsCreighton](https://archiveofourown.org/users/RsCreighton/pseuds/RsCreighton)




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